Metal ion catalysis of the decomposition of transient 2-carboxy-2,5-cyclohexadienones in aqueous solution
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Bromide ion induced debromination of the anion of 4-bromo-4-methyl-2,5-cyclohexadienone-2-carboxylic acid (1) is catalyzed by cupric ions and ferric ions. Similarly, the enolization of the anion of the benzocyclohexadienone 3, which is formed during the bromination of 1-naphthol-2-carboxylic acid, is catalyzed by some metal ions. The origin of the catalysis in these reactions is strong metal ion binding to the incipient dianion products that are of the salicylate type. Evidence for this is that the efficiency of the metal (and hydrogen) ion catalysis parallels the stability of the analogous complexes with the salicylate dianion.
1998 ◽
Vol 53
(8)
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pp. 903-908
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1999 ◽
Vol 64
(4)
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pp. 613-632
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2000 ◽
Vol 55
(12)
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pp. 1141-1152
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2008 ◽
Vol 14
(32)
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pp. 10036-10046
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1998 ◽
Vol 4
(6)
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pp. 1053-1060
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2005 ◽
Vol 102
(21)
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pp. 7459-7464
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